


Care to Help Me Out?

by Falka_tyan



Category: Original Work
Genre: Alternate Universe - BDSM, Caning, Crack Treated Seriously, Discipline, Dom/sub, Friends to Lovers, Happy Ending, M/M, Orgasm Control, Orgasm Delay/Denial, Original Character(s), POV First Person, Punishment, Spanking
Language: English
Status: Completed
Published: 2020-01-05
Updated: 2020-01-05
Packaged: 2021-02-27 09:47:59
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,096
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22135054
Author URL: https://archiveofourown.org/users/Falka_tyan/pseuds/Falka_tyan
Summary: Jill's friend Terry decides that he wants to be a sub instead of staying a switch like 70% of the population. It's his right but isn't it too hard a way to live? Jill isn't sure he understands him.But when Terry comes crying for help, who is Jill to refuse him?Even if it goes about spanking his friend's butt.
Relationships: Original Male Character/Original Male Character
Comments: 8
Kudos: 43





	Care to Help Me Out?

**Author's Note:**

> Dear readers,
> 
> it just happened. I mean, I can't take this fully serious but at the same time I already like these boys.
> 
> So please, be nice to us!

I can see him trembling and biting his lips as soon as he enters the room. Is he here to ask for a spanking, _again_?

“Come on, Terry, come here. Is something the matter?”

“I... I’m sorry, Jill. I… I did it again. I’m sorry,” – he whispers in a barely-there voice.

“What did you, do, Terry?” – I decide to make sure before it’s too late.

Terry comes closer and sits next to me on the couch. He’s so nervous. Unfortunately, I can’t help him here. He knows what happens when he doesn’t follow his rules.

“I jerked off touching my cock and came.”

I gasp as if horrified. Terry winces.

We both know that if he wants to become a good subby this kind of behavior is unimaginable.

“Didn’t you wear your cage, Terry? I know you had it on yesterday morning.”

“I did. I had to go to the doctor’s, and he said he needs it off for some inspection, but he didn’t make me put it back on afterward.”

I tsk and shake my head. The temptation was too strong. If this doctor knew how seriously Terry takes his self-discipline and how much he strives to be a better subby he’d maybe pay attention to that damned cage.

“You’ve been punished just last week, Terry. We know the first year after making your choice is hard but you need to get used to a lack of orgasms. Many Doms prefer to have their subs fully celibate.”

“I know, - nods Terry. – I know, Jill. I try to be good but when I get a chance like that it feels like I can’t miss it, you see? Ah, you wouldn’t understand.”

Terry visibly deflates. He slumps on the couch and looks at the ceiling.

That’s true. I don’t know what he goes through. I only know that as soon as Terry meets his Dom, there’s going to be even more changes. While he’s free, nobody can dictate him what to do with his body. Yet, as soon as he has a contract in place, he’s going to have to go through so many procedures ensuring his faithfulness to his Dom, lose so many freedoms at once, that I fully support his decision to start getting used to his status before that.

“Yes, Terry, I can’t imagine what you’re feeling right now, OK? But I know what you told me before. I remember you persuading me that I need to be tough with you. How you need me close while you’re waiting for your Dom.”

I say what needs to be said. Why do the words feel heavy on my tongue?

Terry answers his: “Yes, Jill” to the ceiling, and things go the same route as usual after that.

We go to my playroom. While I rummage through the dressers, he strips down his pants and leans over the bench. He has a nice round ass. If I were his Dom, though, I’d make him work out more so it would fill out and become a real bubble butt.

I make Terry recite his sins and then start spanking him. First with my bare hand, then with the flogger. I go slowly. Every strike makes Terry quiver and moan. He’s so sensitive there already. What will happen after he has to follow all typical subby routines? Terry will have to be trained to take pain better. His Dom is going to need a lot of patience – Terry doesn’t like challenges. He needs to be coaxed into taking his pain like a good boy…

As if trying to prove me right, Terry starts acting up when it’s time to change positions. Fully naked now, he begs me not to put him on the table, not to tie him up… He does it every time but, as before, I come out on top and bend him to my will.

Later, when Terry is safely strapped to the table, a leather pillow under his hips and a wooden bit in his mouth, I allow myself a moment of rest.

Terry’s ass is red and hot to the touch already. But we know from previous try-outs that Terry responds to a caning better than to anything else. So this is what we’re doing.

Terry is weeping pathetically. Poor boy. It’s a pity that this is exactly what he needs.

I take the cane and tap it over Terry’s buttocks. At this light touch, Terry bucks up, then realizes it was a false alarm and stills.

I pat him on the back in encouragement, then take some oil and spread it over Terry’s ass. The oil will magnify the pain and keep the bruises to a minimum. Well, as much as it’s possible.

Patiently and unhurriedly, I guide my friend Terry through his punishment.

It’s painful, I know. Extremely painful. But it needs to be done.

The first stroke lands across the meatiest part of Terry’s ass, and Terry howls. It’s a good thing the bit gag is strapped to his head. Terry really needs to bite onto something.

The second stroke lands next to the first, making Terry cry out.

Soon, he whimpers non-stop and shouts at every next strike. At the tenth one, I make a little pause to rub more oil into the skin of Terry’s ass cheeks… and buttocks.

“I know, Terry, I know,” – I soothe him when Terry starts agitatedly mumbling something from behind the gag. We didn’t discuss the thigh caning beforehand but I am sure that’s exactly how Terry needs it today.

The eleventh strike falls under the swell of Terry’s ass, catching the previous welts. Terry yowls and thrashes. I am sure that Terry would’ve jumped right off the table if not for his bindings.

“Sh, sh-sh, you’re doing so well, Terry, calm down,” – I reassure him. It doesn’t help immediately. Terry is still fighting the restraints like mad. It’s impressive. I have to wait him out. When Terry is exhausted, I take the gag out and allow Terry to blabber.

“Jill, please, no more! I can’t take it! It’s too much! Ouch, ouch, ouch, please, it hurts! No more, please!” and other similar pleas for mercy fall on deaf ears.

“A good subby knows how to lie still and take it. I am sure this is doable for you. Have faith in yourself, Terry.”

After some time, the pleading is replaced by miserable sobs. I let him cry his fill, then make him drink some water and put the gag back.

“That’s it. Doing so well, Terry. I’m so proud of you,” – I whisper tenderly, rubbing Terry’s lower back in circles.

His ass looks enticing. Red and welted, but not starting to turn blue yet. I am glad I decided to use oil – I’d never have gotten this perfect hue on Terry’s ass otherwise.

“You know you need it, Terry. Yes, don’t argue, you do. I’m so sorry it hurts, dear. You know I do. Let’s get it over with so that I can put your little cock into its cage again and you can get on with your life?”

Said cock is lying on the leather pillow between Terry’s thighs, small and plump. I want to torture it so badly. They say that when subbies finish their hormonal course, their cocks become extremely sensitive. They need the cock cages to defense their tender flesh from touch more than they need them to keep wandering hands away. I had never had the pleasure of seeing an owned subby’s cock without a cage. As rare as they are (the subbies in our society, I mean), it’s not surprising. Only so many people decide to go down that path. I am still baffled by the fact that my friend Terry did.

He’s such a scaredy-cat, he’s so unsure of himself, so passive. Yet, he defended his decision against his parents and his brothers and his teachers. When he came to me once, in tears, ready to be thrown out onto the street because no one wanted to support him anymore, I wanted to say the same thing that everyone else: “It’s hard and painful. It’s not for you, Terry.” Gosh, I’ve almost said it. Almost.

In the end, Terry got to stay at home, his family agreed to honor his decision, only insisting that he gets his degree before settling for a Dom. Terry went to courses for young subs every week and bought himself a cock cage. It looked like his life wouldn’t change drastically.

After several months, he came to me in tears again. Turned out, he “was doing it all wrong, was a bad sub, and was never going to find a Dom”. No reassurances from me did help.

In desperation, I offered what seemed to be the only solution at the moment. This agreement.

This is how we find ourselves where we are: I with a cane in hand and Terry – on a table with a beaten ass.

Speaking of which…

“I need to finish your discipline, Terry,” – I announce and wait for a reaction.

Terry sniffles and says nothing.

“OK, let’s get it over with. Brace yourself.”

The cane swishes through the air and finds its target. Terry moans and keens but doesn’t try to rip the straps off this time. He endures the next eight strikes with dignity, too. I am impressed.

“Your thighs now, Terry. You ready?”

Terry nods.

“That’s a brave boy,” – I praise.

Six strokes to Terry’s thighs pass in a blur. Terry goes a little wild again, jumps up at every impact and wails. I have to coax him into enduring every next stroke as if trying to make him take a bitter pill.

But then, it’s over.

“It’s over, Terry. You’ve managed it. All strikes are over. You took your punishment like a good boy.”

I take the gag out and make him drink. Unfortunately, there are a few technicalities we still need to take care of as well.

“Did you give yourself an enema before coming here?”

“Yes, Jill,” – comes Terry’s hoarse whisper. At the sound of his voice, I realize I’m so aroused I could cry. Well, Terry is, too, but only one of us will get to orgasm today.

“Good, then prepare for your favorite plug.”

The plug is inflatable and will keep Terry uncomfortably full until evening. He doesn’t like it, at all. Yet, this time, he surrenders easily, all fight drained out of him thanks to the previous ordeals.

I lube the plug, stretch Terry a bit, just to be on the safe side, then put the plug inside. It’s slim for now and goes in without issues. I do a quick job of pumping it to its maximum size (as much as I dare), making it as unpleasant for Terry as possible.

Terry starts huffing and breathing through his nose raggedly. My method seems to be working.

“That’s it. Instead of rubbing your dildo inside your ass as you were supposed to, you put your hands on your cock. You knew it was off-limits yet you still did it. It was so naughty of you, Terry, so naughty.”

“I’m sorry, Jill. It won’t happen again,” – Terry sounds genuinely apologetic.

“I sure hope so,” – I reply sternly.

Terry is lucky he’s not wearing a plug made from ginger – I hate the thing too much to use it, even if it’s good for wayward subs. Maybe, I should advise Terry to use it on himself when he feels like getting into trouble.

I clean up my “workplace”, put my implements away and bring the tiny metal cock cage Terry despises so much. Terry has calmed down significantly by the time I unstrap the bindings and help him stand up from the table.

“Sit here, please,” – I say nudging a wooden chair to Terry.

Terry almost starts crying anew as his blistered butt comes in contact with the unforgiving surface.

“Push your legs apart. That’s it. Look at you, all chubbed-up. Your cock certainly agrees that you require spankings, huh?”

“Don’t joke, Jill, please. It’s impolite,” – complains Terry. He’s never as grumpy as when his cock is about to be locked up, which is – fair?

This time, I don’t feel sorry for Terry. I think that Terry’s cock was made to be kept in a cage. So small and insignificant. It’s silly how much Terry loves rubbing it. I want it to always stay locked, suffering from unfulfilled arousal. That’s what Terry needs – to be kept chaste and horny.

Meanwhile, Terry squirms like an eel on a pan on his chair. It must be the plug. Terry always complains that he can’t ever find a comfortable position with it inside.

Well, I am about to help him forget about this inconvenience.

I also take a quick look at Terry’s balls. They’re so small and tight! That’s not how it should be. A subby’s balls need to hang heavy and swollen between their legs, looking unpleasant and even painful.

Now we’re getting to my favorite part. Mine, not Terry’s.

When Terry sees the ice-cold wet towel in my hands (it’s freezing and my palms protest from holding it), his eyes literally fill with tears.

“One more thing, baby,” – I soothe. I don’t know how the endearment slipped out of my mouth.

Terry looks stricken for a second, then nods.

“Keep your legs where they are, - I remind him and get on with it. Terry positively _squeals_ when the towel first touches his testicles. It’s an amazing sound. So rewarding to my ears.

Of course, Terry tries to close his thighs as soon as the process really starts. I tsk. My friend is so impatient. That won’t do. I put the freakishly cold thing down, quickly strap Terry’s ankles to the chair’s legs, give his balls a squeeze in punishment and then start with the towel anew. Terry’s stubborn cock doesn’t want to go down. I even have to use the second cold towel I prepared which leads to more desperate squealing and begging for mercy, until finally, Terry’s cock is defeated and locked securely inside its steely prison.

“That’s it, Terry. All done”.

I help Terry up and give him his clothes. I am supposed to be putting Terry on his knees in a corner right now but we always skip it. It’s no fun, and Terry has many other opportunities to think about his behavior or whatever he is supposed to do in there. In any case, Terry gets restless and nervous from being sent into a corner. That’s not for him. I hope his future Dom will keep it in mind.

We migrate to the kitchen where I make us tea and Terry tries to sit still on his chair. Not once do I have to suppress a smirk. I feel so smug and pleased after I’d given my friend what he needs.

We drink our cups in silence. And what if it’s the ritual I use to replace corner time? We both benefit from it, and no one needs to know.

Later, we stretch out on the carpet in the living room, the TV a pleasant buzz in the background, and talk.

I come down from my high – these sessions with Terry are a damned power trip every single time! Terry seems to calm down, too. We don’t discuss the punishment – Terry knows he will have to write down his impressions for me later today. It’s also one of our unique routines that work.

For now, we’re just friends, again. How it’s supposed to be.

I don’t know why settling into our usual routine is so… disappointing.

I glance at Terry. He is lying on his belly and kicking his legs up and down. He seems pensive, too.

“Terry?” – I try, suddenly worried. What if there’s something that needs to be addressed urgently? I can’t let it slide.

To my astonishment, Terry looks away from me and hides his face in his arms. Is he… blushing?

I don’t know what to make of it. I’d seen Terry in all kinds of compromising states, I’d humiliated him deliberately for the last two years since we’d come to this agreement. Terry flushes all over when he’s about to get spanked, yes, but I had never seen him get red in the cheeks, just like that. It’s so cute that it makes my heart ache.

Then, Terry mutters something into his folded arms.

I can’t catch a word.

“What was that?” – I inquire carefully, afraid to scare him off.

Terry lifts his head a little and mumbles, barely coherent:

“If only you could be my Dom.”

“What? – I react dumbly. It’s so not what I expected to hear! – Could you repeat it, please? Terry?”

But Terry keeps his face hidden and doesn’t say anything else.

My brain shuts down. When it comes back online it’s to the view of Terry’s jeans-clad butt moving to stand up from the ground.

“Terry! Wait!”

My hand shoots up to catch him but I only caress the hem of his pant leg.

Honestly, I’m panicking. I can’t let Terry go now!

“Do you mean it?” – I ask Terry’s back. Good grief, now _I_ sound pathetic.

“I do,” – confirms Terry, looking ahead of himself.

I can’t believe what I’m hearing.

Luckily, this time my mouth runs ahead of my stupid brain:

“I would have to register our couple, and then, since I’m a switch in a binding relationship with a sub, they’d require that I have public spankings at the Community Centre twice a year, and…”

Terry whirls around, mouth agape, and interrupts my babbling.

“You’d do it? For me?”

“For me, Terry! For me! I never wanted to let you leave me behind and find someone else to take care of you one day!”

The next second I tumble to the ground under Terry’s weight. Terry basically pins me down by the wrists and kisses me, hard.

When Terry comes up for air, he continues keeping me down and announces:

“If you change your mind it’ll be too late! There’s no way back for you! You’ll have to be the one taking me to therapy and doing all those despicable things to me! And enduring my mood swings! And taking care of my many obligatory piercings! All these things done to a subby, and you gonna try every single one on me!”

And then he smashes our mouths together again.

“That’s the subbiest sub you’ll ever meet,” – I think, dazedly. But call me a sap, I’d never have it any other way, with any other person.

**Author's Note:**

> Phew!  
> What do you say about their future? - I personally think they're going to be just fine!
> 
> Come to my Twitter! It's [Falka-tyan](https://twitter.com/FalkaTyan/)  
> or my Tumblr: [Falka-tyan](http://falka-tyan.tumblr.com/)


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